Host Gerry Scott sits down with Heather Sanders of Tax Junction, a cross-border personal tax specialist who helps U.S. citizens living in Canada and Canadians working for U.S. employers navigate the complexities of filing in two countries at once.

With a practice built around real people in real cross-border situations, not corporations or trusts, Heather brings practical, ground-level insight into the mistakes that happen when employees move countries without thinking through the tax consequences first, and what it actually takes to get it right.

Together, Gerry and Heather unpack some of the most misunderstood rules facing cross-border workers, including why "I just work from my home office" is never as simple as it sounds, and why the payroll question matters more than most people realize.

In this conversation, they explore:

• Why the country where you physically work determines where your payroll must be registered, and the liability risk employers face when it isn't

• The Certificate of Coverage and when Canadians working for U.S. companies can still contribute to CPP

• How 401(k) contributions are treated in Canada and why aligning them with your RSP room is the key to avoiding a surprise tax bill

• Why RSP contributions aren't deductible on a U.S. return, and why that usually matters less than people fear

• The risks of large catch-up RSP contributions for U.S. citizens living in Canada

• How mid-year payroll switches between W-2 and T-4, especially when RSUs are involved, can create reporting nightmares

• Why selling U.S. real estate as a Canadian non-resident requires the right people in your corner from the start

• The foreign tax credit audit that CRA triggers more often than most people expect, and what happens when no one responds

• Why "my situation is pretty straightforward" is almost never true once a border is involved

If you're living in Canada and working for a U.S. employer, considering a cross-border move, or simply trying to understand what compliance actually looks like for internationally mobile workers, this episode offers a frank and practical look at the planning that protects you and the mistakes that are far easier to avoid than to fix.
Cross-border tax doesn't have to be overwhelming. Download the Snowbirds DayTracker app today to connect with specialists like Heather and access the tools and resources you need to navigate your international life with confidence.

In this episode of the Snowbirds Expat Radio, host Gerry Scott welcomes back cross border tax specialist Sharon Conrod of Hanson Tax LLC for a timely conversation on one of the most misunderstood cross border situations today Canadians living in Canada while working for U.S. employers.

As more professionals take U.S. roles while residing north of the border questions around 401k plans IRAs RRSP room and treaty relief are becoming increasingly common and increasingly complex. Sharon explains how U.S. retirement plans are treated in Canada when deductions are available why tracking basis matters and where many people unknowingly create future tax issues.

The discussion also explores remote work considerations employer matching crystallization strategies state level tax risks and why there is truly no one size fits all solution when families live and work across borders.

What You Will Learn

• How 401k and IRA contributions are treated when you live in Canada

• When U.S. retirement contributions may or may not be deductible in Canada

• Why RRSP room limits matter for cross border commuters

• The role of Form RC268 and why it is critical for Canadians with U.S. plans

• How employer matching works and when it still makes sense to participate

• Why tracking non deductible contributions over time is important

• How crystallizing RRSPs before moving to the U.S. can reduce future taxes

• Why certain U.S. states can complicate otherwise treaty protected plans

• Common mistakes remote workers and employers make

• Why residency and family dynamics matter in cross border planning

Why This Episode MattersCross border work arrangements have grown significantly but the tax rules have not become any simpler. This episode highlights why working with experienced cross border professionals can help prevent costly mistakes both now and in the future.

In this episode of the Snowbirds Expat Radio Podcast, host Gerry Scott welcomes back returning guest Aaron Dawes, a cross-border personal tax expert with Smythe.

While previous conversations focused on Canadians heading south, this discussion flips the script. With shifting economic, political, and lifestyle factors, more Canadians—and Americans—are now moving north, returning to or relocating to Canada despite weather, cost, and lifestyle tradeoffs.

Aaron explains what’s driving this trend and what individuals need to consider before making the move, especially when it comes to cross-border tax exposure.

In this conversation, Gerry and Aaron discuss:

• Why more Canadians are returning home from the U.S.

• What’s motivating Americans to relocate to Canada

• How lifestyle, stability, and long-term planning factor into relocation decisions

• The tax implications of moving between the U.S. and Canada

• Why cross-border tax planning is critical before you move

• Common mistakes people make when changing tax residency

• How working with a specialist can prevent costly surprises

With decades of experience handling U.S.–Canada personal tax matters, Aaron offers practical insights for snowbirds, expats, and globally mobile families navigating an increasingly complex cross-border landscape.

If you’re considering a move—or a move back—this episode highlights why planning ahead matters more than ever.

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

Connect with Aaron Dawes